Antibacterial condensed thiazoles

1. A compound of formula (I) or a salt or N-oxide thereof:

wherein:

m is 0 or 1;

Q is hydrogen or cyclopropyl;

Alk is an unsubstituted C 1 -C 6 alkyl;

X is —C(═O)NR 6 —, or —C(═O)O— wherein R 6 is hydrogen, optionally substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;

Z 1 is —N═ or —CH═

Z 2 is —N═ or —C(R 1 )═;

R 1 is hydrogen, methyl, ethyl, ethenyl, ethynyl, methoxy, mercapto, mercaptomethyl, halo, fully or partially fluorinated (C 1 -C 2 )alkyl, (C 1 -C 2 )alkoxy or (C 1 -C 2 )alkylthio, nitro, or nitrile (—CN);

R 2 is a group Q 1 -[Alk 1 ] q -Q 2 -, wherein

q is 0 or 1;

Alk 1 is an optionally substituted, divalent, straight chain or branched C 1 -C 6 alkylene, or C 2 -C 6 alkenylene or C 2 -C 6 alkynylene radical which may contain or terminate in an ether (—O—), thioether (—S—) or amino (—NR)— link;

Q 2 is an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 5 or 6 ring atoms or an optionally substituted divalent bicyclic carbocyclic or heterocyclic radical having 9 or 10 ring atoms;

Q 1 is hydrogen, an optional substituent, or an optionally substituted carbocyclic or heterocyclic radical having 3-7 ring atoms.

2. A compound as claimed in claim 1 wherein Z 1 is —CH═.

3. A compound as claimed in claim 1 wherein Z 2 is —CH═.

4. A compound as claimed in claim 1 wherein Z 2 is —CF═.

5. A compound as claimed in claim 1 wherein Z 1 and Z 2 are both —CH═.

6. A compound as claimed in claim 1 wherein Z 1 is —CH═ and Z 2 is —CF═.

7. A compound as claimed in claim 1 wherein m is 1 and Q is hydrogen.

8. A compound as claimed in claim 1 wherein X is —C(O)NH—.

9. A compound as claimed in claim 1 wherein m is 1, Q is hydrogen, Alk is —CH 2 CH 2 —, and X is —C(O)NH—.

10. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Q 2 is an optionally substituted pyridine, pyrimidine, pyrazine, pyran-2-one, pyrimidine-4-one or pyridine-2-one ring.

11. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Q 2 is an optionally substituted pyridine-3-yl ring, an optionally substituted pyrimidine-5-yl ring, an optionally substituted pyrazine-2-yl ring, an optionally substituted pyran-2-one-4-yl ring or an optionally substituted pyridine-2-one-4-yl ring.

12. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Alk 1 is present and is an optionally substituted divalent C 1 -C 3 alkylene radical.

13. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Q 1 is a group of formula —NR A R B , wherein R A and R B are independently hydrogen or a (C 1 -C 6 )alkyl, hydroxy(C 1 -C 6 )alkyl, or (C 1 -C 3 )alkoxy(C 1 -C 3 )alkyl group.

14. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Q 1 is a group of formula —NR A R B , wherein R A and R B taken together with that nitrogen form a cyclic amino ring.

15. A compound as claimed in claim 1 wherein the cyclic amino ring is a morpholinyl, piperidinyl, or piperazinyl ring.

16. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Q 2 is an optionally substituted pyridinyl, pyrimidinyl or pyrazinyl radical, q is 0 and Q 1 is an optionally substituted heterocyclic radical having 3-7 ring atoms.

17. A compound as claimed in claim 16 wherein Q 1 is an optionally substituted oxadiazolyl or tetrazolyl radical.

18. A compound as claimed in claim 16 wherein Q 1 is an optionally substituted piperidinyl or pyrrolidinyl radical.

19. A compound as claimed in claim 18 wherein Q 1 is substituted by —COOH.

20. A compound as claimed in claim 1 wherein, in the substituent R 2 of the said compound, Q 2 is an optionally substituted pyrimidine-4-one or pyridine-2-one, q is 1 and Q 1 is an optionally substituted heterocyclic radical having 3-7 ring atoms.

21. A compound as claimed in claim 20 wherein, Alk 1 is —CH 2 — and Q 1 is an optionally substituted pyridinyl radical.

22. A compound as claimed in claim 1 selected from the group consisting of:

1-ethyl-3-(5-pyridin-3-yl-benzothiazol-2-yl)-urea

2-{5-[2-(3-ethyl-ureido)-benzothiazol-5-yl]-pyridin-2-yl}-N-methyl-acetamide

1-ethyl-3-[5-(1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-benzothiazol-2-yl]-urea

1-ethyl-3-(6-fluoro-5-pyridin-3-yl-benzothiazol-2-yl)-urea

1-(5-([1,2,4]triazolo[4,3-a]pyridin-6-yl)benzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(5-(imidazo[1,2-a]pyridin-6-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(tetrazolo[1,5-a]pyridin-6-yl)benzo[d]thiazol-2-yl)urea

1-(5-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)benzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(5-(6-(hydroxymethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(5-(2-oxopyridin-1(2H)-yl)pyrazin-2-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(2-(hydroxymethyl)-1-methyl-1H-imidazol-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-2-(5-(2-(3-ethylureido)benzo[d]thiazol-5-yl)-2-oxopyridin-1(2H)-yl)acetate

1-(5-(1-(2-ethoxyethyl)-6-oxo-1,6-dihydropyridin-3-yl)benzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(5-(6-methyl-2-oxo-2H-pyran-4-yl)benzo[d]thiazol-2-yl)urea

methyl 5-(2-(3-ethylureido)benzo[d]thiazol-5-yl)picolinate

1-ethyl-3-(5-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)urea

1-(5-(1H-pyrazol-3-yl)benzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(5-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(isoquinolin-4-yl)benzo[d]thiazol-2-yl)urea

1-(5-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(5-(2-methoxythiazol-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(2-hydroxythiazol-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(imidazo[1,2-a]pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-(5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)benzo[d]thiazol-2-yl)-3-ethylurea

N-(5-(2-(3-ethylureido)benzo[d]thiazol-5-yl)pyridin-2-yl)acetamide

1-ethyl-3-(5-(6-morpholinopyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-(5-(2-(1H-imidazol-1-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(5-(2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(1-(2-methoxyethyl)-6-methyl-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(1-(2-hydroxyethyl)-6-methyl-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(6-methyl-1-((6-methylpyridin-2-yl)methyl)-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(6-methyl-2-oxo-1-(pyridin-3-ylmethyl)-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(6-methyl-2-oxo-1-(pyridin-2-ylmethyl)-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(5-(6-methyl-2-oxo-1-(1-(pyridin-2-yl)ethyl)-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

ethyl 7-(2-(3-ethylureido)benzo[d]thiazol-5-yl)-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

N-(5-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)pyridin-2-yl)acetamide

ethyl 2-(4-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)-1H-pyrazol-1-yl)acetate

1-ethyl-3-(6-fluoro-5-(6-methyl-2-oxo-2H-pyran-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(2-(4-(2-hydroxyethyl)piperazin-1-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(2-(piperazin-1-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)urea hydrochloride salt

methyl 1-(5-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate

1-(5-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylic acid

methyl 1-(5-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-3-carboxylate

1-(5-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-3-carboxylic acid

methyl 2-(4-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)-1H-pyrazol-1-yl)propanoate

1-ethyl-3-(6-fluoro-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(6-methyl-2-oxo-1-(pyridin-3-ylmethyl)-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(6-methyl-1-((1-methylpyrrolidin-3-yl)methyl)-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(6-methyl-1-((1-methylpiperidin-2-yl)methyl)-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(6-methyl-1-((1-methyl-1H-imidazol-4-yl)methyl)-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

tert-butyl 2-((4-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)-6-methyl-2-oxopyridin-1(2H)-yl)methyl)pyrrolidine-1-carboxylate

1-(5-(1-(3-(dimethylamino)propyl)-6-methyl-2-oxo-1,2-dihydropyridin-4-yl)-6-fluorobenzo[d]thiazol-2-yl)-3-ethylurea

1-ethyl-3-(6-fluoro-5-(6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-[6-fluoro-5-(4-methoxy-pyridin-2-yl)-benzothiazol-2-yl]-urea

1-ethyl-3-(6-fluoro-5-(2-(4-methylpiperazin-1-yl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(5-methoxypyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(5-hydroxypyridin-3-yl)benzo[d]thiazol-2-yl)urea

5-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)-N′-hydroxypicolinimidamide

1-ethyl-3-(6-fluoro-5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(1-(2-morpholinoethyl)-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-(5-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2-dihydropyridin-4-yl)-6-fluorobenzo[d]thiazol-2-yl)-3-ethylurea

tert-butyl 3-((4-(2-(3-ethylureido)-6-fluorobenzo[d]thiazol-5-yl)-2,2′-dioxo-2H-1,4′-bipyridin-1′(2′H)-yl)methyl)piperidine-1-carboxylate

1-ethyl-3-(6-fluoro-5-(6-(hydroxymethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(6-(morpholinomethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(2-oxo-1-(pyrrolidin-3-yl)-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

2-{5-[2-(3-ethyl-ureido)-6-fluoro-benzothiazol-5-yl]-pyridin-2-yl}-N-methyl-acetamide

1-ethyl-3-(6-fluoro-5-(thiazol-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-fluoro-5-(2-(methylsulfonyl)pyrimidin-5-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-methoxy-5-(pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-methoxy-5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-methyl-5-(pyridin-3-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-methyl-5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)benzo[d]thiazol-2-yl)urea

1-ethyl-3-(6-(pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)urea

N-(5-(2-(3-ethylureido)thiazolo[5,4-b]pyridin-6-yl)pyridin-2-yl)acetamide

1-ethyl-3-(6-(6-methyl-2-oxo-2H-pyran-4-yl)thiazolo[5,4-b]pyridin-2-yl)urea

1-Ethyl-3-(6-fluoro-5-{6-methyl-1-[1-(6-methyl-pyridin-3-yl)-ethyl]-2-oxo-1,2-dihydro-pyridin-4-yl}-benzothiazol-2-yl)-urea and

1-Ethyl-3-{6-fluoro-5-[1-(3-methoxy-pyridin-2-ylmethyl)-2-oxo-1,2-dihydro-pyridin-4-yl]-benzothiazol-2-yl}-urea.

23. An antibacterial composition comprising a compound as claimed in claim 1 , together with one or more pharmaceutically acceptable carriers and/or excipients.